- Kevin Sanders
- Mar 15
- 3 min read
March 15, 2025
Read Time - 4 minutes
When I first sat down with a coach years ago, I thought I needed to prove something. I’d prepared answers. I had a list of goals. But what actually helped most was learning to pause, reflect, and tell the truth about what I really needed as a leader. That first session? It wasn’t what I expected—but it was exactly what I needed.
Feeling Nervous? That’s Normal.
Starting executive coaching can feel like opening a new chapter in your leadership story. But if you don’t know what to expect, it’s easy to over-prepare—or worse, under-value the opportunity.
Let’s take the mystery out of that first session.
Whether you’re a new dean, a department chair considering coaching for the first time, or a seasoned leader seeking clarity, here’s what typically happens in Session One—and how to show up ready.
What Happens in Your First Coaching Session?
Your first executive coaching session is about you—but not in a vague, talk-about-yourself way. It’s structured, thoughtful, and meant to open up new clarity. Here’s what’s usually on the agenda:
1.Goal Setting
You’ll be asked what you hope to get out of coaching. Some leaders bring clear goals (“I need to improve delegation”). Others are in transition or feeling stuck. Either way, expect questions like:
What would success look like in 6 months?
Where are you feeling tension or misalignment right now?
2.Context Discovery
Coaches want to understand your world: your team, your role, your institutional landscape. Not to give you advice—but to tailor the coaching to you. Expect questions like:
Who are your key stakeholders?
What’s changing around you right now?
What kind of leader do you want to become?
3.Process and Expectations
You’ll clarify how coaching works.
What does confidentiality look like?
Will you get homework or tools between sessions?
How will progress be tracked?
Coaching Isn’t Therapy...or a Performance Review.
It’s easy to assume coaching is about fixing something that’s broken—or proving your worth. It’s not.
Coaching is a space for honest reflection, powerful questions, and intentional growth.
This isn’t a therapy session. You won’t be asked to unpack your childhood.
It’s also not a performance review—no one is grading you.
Instead, think of it as a thought partnership built on curiosity, trust, and growth.
Common Coaching Questions
Don’t be surprised if your coach asks questions like:
What’s the conversation you’re avoiding?
What’s one decision you’ve been putting off?
If nothing changes, what’s at risk?
These questions aren’t meant to put you on the spot. They’re designed to uncover blind spots, challenge assumptions, and help you make better decisions faster.
How to Prepare for Your First Coaching Session
You don’t need a PowerPoint. But a little reflection goes a long way.
Here’s how to get the most from your first meeting:
✅ Jot down 1–2 leadership challenges you’re facing right now
✅ Name a win you’re proud of from the last year
✅ Be honest about where you feel unclear, under-resourced, or stuck
✅ Bring curiosity, not conclusions—this is about discovery
The Bottom Line
Your first coaching session isn’t about performance—it’s about perspective.
It’s a space where you can pause the noise, think out loud, and start designing the kind of leadership you want to grow into.
Whether you leave with a plan, a question, or a shift in how you see your role, it will move you forward.
Because great leaders aren’t just busy—they’re intentional.
And coaching helps you get there.
Try This Before Friday
Block 20 minutes on your calendar. Ask yourself:
What’s one leadership challenge that’s consuming more of your time than it should?
Write down why it matters—and what you’ve already tried.
That’s your perfect first coaching conversation.
👥 Ready to Help Others?
This goes out each week to leaders trying to build better systems, stronger teams, and healthier departments. If this helped you navigate your corner of campus, pass it on! 👉 Subscribe here.
Whenever you're ready, there are 3 ways I can help you:
1.) Get the free guide: Lead by Design. Put an end to reactive leadership. Learn how to clarify decisions, streamline workflows, and surface expectations—so you can fix what’s broken and focus on what matters most. 2.) Coaching for Academic Leaders: A focused 1:1 coaching experience for higher ed professionals who want to lead with clarity, build smarter systems, and stay centered on what matters most. I work with a limited number of clients each quarter to provide highly personalized, strategic support. Send me a message. 3.) Professional Development Workshops: Interactive sessions for faculty, staff, and leadership teams that help reduce conflict, streamline decision-making, and shift culture with smart systems. Virtual and in-person options available. Sessions tailored to your campus needs. |